Reactions that form carbon-carbon (C-C) and carbon nitrogen (C-N) bonds via the direct oxidative coupling of two carbon-hydrogen (C-H) or nitrogen-hydrogen (N-H) bonds are valuable tools for the organic synthesis of biologically active molecules. The three proposed projects involve either the synthesis of biaryls via oxidative coupling of two sp2-hybridized C-H bonds or oxidative amination via the direct coupling of an sp2-hybridized C-H with the N-H of phthalimide. Significant preliminary results have been generated for each of the processes. In each case, hypothesis-driven mechanistic investigations are proposed. The accomplishment of the proposed work will provide organic chemists with new paradigms, through which they can envision synthetic routes to complex target molecules. PUBLIC HEALTH RELEVANCE: This proposal describes the development of new chemical reactions that simultaneously cleave two carbon-hydrogen bonds or nitrogen-hydrogen bonds and couple them to form carbon-carbon bonds or carbon-nitrogen bonds. This technology will streamline the synthesis of organic molecules, such as pharmaceuticals, by reducing the number of chemical derivations that are required to form carbon-carbon bonds, as well as reducing the hazardous waste associated with organic synthesis. Additionally, the application of this technology to the synthesis biaryl peptides, an important class of bioactive natural products, is proposed.